N-ARYLTHIOCARBAMATES, HERBICIDES QUI EN CONTIENNENT, ET PROCEDES POUR COMBATTRE LA CROISSANCE DE PLANTES INDESIRABLES A L'AIDE DE CES PRODUITS

N-ARYLTHIOCARBAMATES, HERBICIDES CONTAINING THEM, AND PROCESSES FOR COMBATING THE GROWTH OF UNWANTED PLANTS WITH THESE COMPOUNDS

Abrégé anglais

ABSTRACT OF THE DISCLOSURE: N-Arylthiolcarbamates for the
formula
<IMG> ,
where R denotes methyl or ethyl, X denotes halogen, Y denotes
alkyl, haloalkyl of at least 2 carbon atoms, alkoxyalkyl, cyclo-
alkyl, alkoxy or halomethoxy, and n denotes one of the integers
1 and 2, herbicides containing these compounds, and their use
as herbicides.

Revendications

O.Z. 0050/033878
The embodiments of the invention in which an exclusive property
or privilege is claimed are defined as follows:
1. An N-arylthiolcarbamate of the formula
<IMG> ,
where R denotes methyl or ethyl, X denotes halogen, Y denotes
alkyl, haloalkyl of at least 2 carbon atoms, alkoxyalkyl, cyclo-
alkyl, alkoxy or halomethoxy, and n denotes one of the integers
1 and 2.
2. An N-arylthiolcarbamate selected from the group consisting
of S-methyl-N-(3-chloro-4-isopropylphenyl)-thiolcarbamate,
S-methyl-N-(3-chloro-4-(1-chloroisopropyl)-phenyl)-thiolcarbamate
and S-methyl-N-(3-chloro-4-(difluoromethoxy)-phenyl)-thiol-
carbamate.
3. A process for combating unwanted plant growth, wherein
the plants or the soil are treated with an N-arylthiolcarbamate
of the formula
<IMG> ,
where R denotes methyl or ethyl, X denotes halogen, Y denotes
alkyl, haloalkyl of at least 2 carbon atoms, alkoxyalkyl, cyclo-
alkyl, alkoxy or halomethoxy, and n denotes one of the integers
1 and 2.
41

Description

~13Z599
O.Z. 0050/033878
N-ARYLTHIOLCARBAMATES~ HERBICIDES CONTAINING THEM, AND PROCESSES
FOR COMBAmING THE GROWTH OF UNWANTED PLANTS WITH T~ESE COMPOUNDS
The present invention relates to novel N-arylthiolcarbamates,
herbicides containing these compounds as active ingredients,
and a process for combating unwanted plant growth with these
compounds.
The herbicidal properties of S-methyl-N-(3-chlorophenyl)-
-thiolcarbamates have been disclosed (U.S. 2,863,899). This
2C compound has only a poor herbicidal action on higher plants.
; We have now found that novel N-arylthiolcarbamates of the
formula
n ~ n
~ NH-C-SR
Y

113Z5~9
o. z . 0050/033878
where R denotes methyl or ethyl, X denotes halogen (chlorine,
bromine, fluorine, iodine), Y denotes alkyl (e.g., methyl,
ethyl, isopropyl, t-butyl, n-hexyl), haloalkyl of at least
2 carbon atoms (e.g., 1-chloroisopropyl, 2-chloroethyl, chloro-
-tert-butyl), alkoxyalkyl (e.g., methoxymethyl, isopropoxymethyl,
2-methoxyethyl), cycloalkyl (e.g., cyclopropyl~ cyclopentyl,
cyclohexyl), alkoxy (e.g., methoxy, ethoxy, n-propoxy, isopropoxy),
or halomethoxy (e.g., difluoromethoxy, trifluoromethoxy) and
n denotes one of the integers 1 and 2, have a surprisingly good
action on a number of broadleaved and grassy unwanted plants
and are tolerated by crop plants.
The two processes described below are for instance suitable
for the manufacture of the new compounds.
~ CO NHCOSR
A ~ HSR ~ ~
Y Xn Y Xn
The reaction of aryl isocyanates with mercaptans takes place
2C in the presence or the absence of a catalyst conventionally used
for isocyanate reactions, e.g., tertiary amines (triethylamine,
1,4-diazabicyclo-(2,2,2)-octane, nitrogenous heterocycles
(pyridine, 1,2-dimethylimidazole) or organic tin compounds
(dibutyl tin diacetate, dimethyl tin dichloride), if desired in
a solvent inert under the reaction conditions, for example
hydrocarbons (e.g., ligroin, gasoline, toluene, pentane, cyclo-
hexane), halohydrocarbons (e.g., methylene chloride, chloroform,
dichloroethane, chlorobenzene, o-, m- and p-dichlorobenzene),

O.Z. 0050/033878
nitrohydrocarbons (e.g., nitrobenzene,nitromethane), nitriles
(e.g., acetonitrile, butyronitrile, benzonitrile), ethers (e.g.,
diethyl ether, tetrahydrofuran, dioxane), esters (e.g., ethyl
acetate, methyl propionate), ~etones (e.~., acetone, methyl ethyl
ketone) or amides (e.g., dimethylformamide, formamide), at from
-30 to +150C, preferably from 0 to 40C, in equivalent
amounts or with one of the reactants in excess (S. Petersen,
Methoden der Organ. Chemie, VIII, p. 131, Georg Thieme-Verlag,
Stuttgart, 4th ed., 1952).
NH2 NHCOSR

Xn
Aromatic amines are reacted with thio chloroformates in a
solvent, e.g., water, alcohols (e.g., methanol, ethanol, iso-
propanol) or as given under A, with the aid of a conventional
acid binder, e.g., alkali metal hydroxides, carbonates or bi-
carbonates, alkaline earth metal oxides, hydroxides, carbonates
2C or bicarbonates, or tertiary organic bases (e.g., triethylamine,
pyridine, N,N-dimethylaniline, N,N-dimethylcyclohexylamine,
quinoline and tributylamine), at from -20 to +150C, preferably
from 20 to 60C. Process B is preferred (German Laid-Open
Application DE-OS 1,643,763).
The preparation of the novel N-arylthiolcarbamates is
illustrated by the following examples.

113Z5~9
O.Z. 0050/033878
EXAMPLE
At 0C, a solution of 4.1 parts by weight of methylmercaptan
and one drop of triethylamine in 40 parts by weight of aceto-
nitrile is dripped into a solution of 12.5 parts by weight of
3-methyl-4-fluorophenyl isocyanate in 200 parts by weight of
toluene. The mixture iS slowly allowed to heat Up to room tem-
peratUre, the solvents are evaporated in a rotary evaporatcr, and
the residue is recrystallized from cyclohexane. White crystals
are obtained which melt at 98-99C (no. 1).
The compound has the following structural formula:
F ~ NHCOSCH3
CH3
EXAMPLE 2
100 parts by weight of sodium bicarbonate is added to
135 parts by weight of 3-chloro-4-isopropylanilinein 1,000 parts
by weight of tetrahydrofuran. While stirring, 89 parts by weight
of thiomethyl chloroformate is dripped in at room temperature
2C (20C), the mixture is stirred for a further 16 hour~ at room
temperature and then filtered, the solvent is distilled off in
a rotary evaporator, and petroleum ether is added to the oil
Which iS obtained. The crystals which form are filtered off and
dried; m.p.: 116-118C (no. 2).

. 113Z599 o.z. 0050/033878
The compound has the following structural formula:
CH3 ~ /--~ ,,
CH ~ NHC-S-CH3
CH
3 Cl
The following N-arylthiolcarbamates may be prepared
analogously:
2C

1~3~9
O.Z~ 0050/033878
X H O
n~r_~ , "
~ N-C-S-~
/
. Y
No X Y Rm.p~. C
3 3-C1 4-CH(CH3)2 C2Hshigh-ly-~scous oi
4 3-Cl 4-CH3 CH3112-113
4-C1 3-CH3 CH3105-107
6 3-Br 4-CH(CH3)2 CH3
7 3-F 4-CX(CH3)2 CH3
8 3-I 4-CH(CH3)2 CX3
9 3-Cl 4-cyclo C5Hg CX3
3-C1 4 C~2CH2Cl CH3
11 3-Cl 4-CzH5 C~393- g5
12 - 4-F. ~-c~3 C2H5
13 3-Cl 5-CH3 c~3127-129
14 3-Br 4-CH(CH3)2 C2H~
3-I 4 C2H5 CH3
16 3-~ 4-C(CH3)3 C2H5
17 3-Cl 4-cyclo C6H11 3
18 3-C1 4-CX(CH~)~CH2Cl) CX377- 79
2C 19 3-Cl 4 CH2CH2G1 C2H5
4_I 2-CH3 CH3
21 3-Cl 4-CH(CH3)(CH20CH3) CH3
22 3-Br 4-CH3 CX3
23 3-C1 4-cyclo C3H5 CX3
24 3-F 4-CH3 CH3122-124
3-C1 4-C(CH3)3 CH3125-127
26 2-F 4-CH3 c~3
27 3-Br CH20CH3 CX3
28 4-C1 3-CE~OC(CH3)3 CH3
-- 6 --

~13Z~9 o. z .oo50/033878
N~. X Y R mL~.C
29 3-Cl 4-i-C5H11 CH3 74~ 76
4-Cl 3-CHtC~3)2 CH3
31 4-Br 3~-CH20C(CX3)3 3
32 3-Cl 4-CH20CH(CH3)2 3
33 3-Br 4-CH20CH(cH3)2 3
34 3-Br 4-n-C3H7 CH3
35. 4-Cl 3-C(CH3)3 CH3
36 4-Br 3-CH(CH3)2 C 3
37 4-Cl 3 CH2CCH3 CH3
38 3-Cl ( 3)( 2 5) CH3 83- 85
39 4-Cl 3 C2H5 CH3
3-Br 4 C2H5 3
41 3-Br 4-C(CH3)2(C2Hs) 3
42 4-Br 3-CH3 3 9 99
43 3-Cl 4-CH2CH20CH3 CH3
44 3-C1 4-n-C3H7 3
45 3-Br 4-CH2CH20CH3 3
46 3-~r 4-C(CH3~ CH3
47 2-F 5-5H3 CH3
48 3-C1 H( H3)( 2 5)C2H5 70- 72
49 3-C1 4-n-c4Hg 3
50 3-~r 4-cyclo CsH11 3
2C 51 3-Cl 4-C(CH3)2(C2H5)CH3
52 2-F 5-C(CH3)3 C~3 38- 40
53 3-Cl 4-n-C5H9 CH~
54 3-Cl 4-OCF2H CH3 98-100
55 3-C1 4-oCF3 CH3
56 4-Cl 3-OCP2H CH3
573-C1 4-OCH3 CH3 130-132
583-~r 4-OCH3 3
593-C1 4-OC2H5 CH3
603-Cl; 4-C1 5-CH3 CH3 144-146
613 Cl 4-OCP3 2 5

1132599
O.Z. 0050/033878
X Y R m.~_ C
623-C1 4-o-i-C3H7 CH3 108-lC9
6~3-C1 4_o_n_C3H7 CX3 104-;06
643-Cl 4-0-i-C3H7 C2H5
653-~1 4-0-n C H C2H5
663-C1, 5-C1 4-O~H3 CH3 162-164
673-C1 4-oCXF2 C2H5
683-Br 4-oC2H5 CH3
693-Br 4-0-n-C3H7 CH3
703-Br, 5-&1 4-OCH3 CH3 161-163
713-Br l'-0-i-C3H7 CX3
- The influence of various representatives of the compounds
according to the invention on the growth of unwanted and crop
plants is demonstrated in greenhouse experiments.
The vessels employed were plastic flowerpots having a
volume of 300 cm3, and which were filled with a sandy loam con-
taining about 1,5% humus. The seeds of the test plants (cf.
Table 1) were sown shallow, and separately, according to species,
and the plants were grown to a height of 3 to 10 cm before being
treated. Certain test plant species were first grown as seedlings
2C in special seedling containers before being transferred to the
abovementioned vessels. The plants were treated with the chemical
agents a few days after they had taken root. The compounds were
emulsified or suspended in water as vehicle~ and sprayed through
finely distributing nozzles onto the plants. The pots were set
up in the greenhouse - species from warmer areas at from 25 to
40C, and species from moderate climates at 15 to 30C. The
experiments were run for from 3 to 6 weeks. During this period,

11325~9
O.Z. 0050/033878
the plants were tended and their reactions to the various
treatments assessed. The scale used for assessment was 0 to 100,
0 denoting no damage or normal emergence, and 100 denoting
nonemergence or complete destruction of at least the visible
plant parts.
The tables which follow demonstrate the selective herbicidal
action of the compounds according to the invention. They are
applied predominantly postemergence, but an action on preemergence
application (i.e., before the plants germinate) is also evident.
A special application technique is to spray to active
- ingredients weith the aid of spraying equipment in such a way
that the leaves of sensitive crop plants ~re if possible not hit;
the active ingredients reach the soil or unwanted plants growing
below the crop plants (post-directed, lay-by treatment). The
application rates vary, depending on season and growth stage,
from 0.1 to 15 kg/ha and more; higher rates are particularly
suitable for total elimination of vegetation.
The herbicidal agents contain from 0.5 to 95, and preferably
from 1 to 90, wt% of active ingredient.
2C In vie~ of the many application methods possible, the agents
according to the invention, or mixtures containing them, may be
used in addition to the crop plants listed in the tables in a
large number of other crops for eliminating unwanted growth.
The following crop plants are given by way of example:

2 5~ ~
O.Z. 0050/033878
Botanical name _ _ Common name
Allium cepa onions
Ananas comosus pineapples
Arachis hypogaea peanuts (groundnuts)
Asparagus officinalis asparagus
Avena sativa oats
Beta vulgaris spp. altissima sugarbeets
Beta vulgaris spp. rapa fodder beets
Beta vulgaris spp. esculenta table beets, red beets
10 ~rassica napus var. napus rape
- Brassica napus var. napobrassica
Brassica napus var. rapa turnips
Brassica rapa var. silvestris
Camellia sinensis tea plants
Carthamus tinctorius safflower
Carya illinoinensis pecan trees
Citrus limon lemons
Citrus maxima grapefruits
Citrus reticulata
2C Citrus sinensis orange trees
Coffea arabica (Coffea canephora,
Coffea liberica) coffee plants
Cucumis melo melons
Cucumis sativus cucumbers
Cynodon dactylon Bermudagrass in turf and lawns
Daucus carota carrots
Elais guineensis oil palms
Fragaria vesca strawberries
-- 10 --

~132599
O.Z. 0050/033878
Botanical name Common name
Glycine max soybeans
Gossypium hirsutum
(Gossypium arbQreum cotton
Gossypium herbaceum
Gossypium vitifolium)
Helianthus annuus sun~lowers
Helianthus tuberosus
Hevea brasiliensis rubber plants
Hordeum vulgare barley
Humulus lupulus hops
Ipomoea batatas sweet potatoes
Juglans regia walnut trees
Lactuca sativa lettuce
Lens culinaris lentils
Linum usitatissimum flax
Lycopersicon lycopersicum tomatoes
Malus spp. apple trees
Manihot esculenta cassava
Medicago sativa al~alfa (lucerne)
2C Mentha piperita peppermint
Musa spp. banana plants
Nicothiana tabacum tobacco
(N. rustica)
Olea europaea olive trees
Oryza sativa rice
Panicum miliaceum
Phaseolus lunatus limabeans
Phaseolus mungo mungbeans
Phaseolus vulgaris snapbeans, green beans,
dry beans
-- 11 --

11;3Z5~3
o. z . 0050/033878
Botanical name Common name
Pennisetum glaucum
Petroselinum crispum parsley
spp. tuberosum
Picea abies Norway spruce
Abies alba fir trees
Pinus spp. pine trees
Pisum sativum English peas
Prunus avium cherry trees
Prunus domestica plum trees
Prunus dulcis almond trees
Prunus persica . peach trees
Pyrus communis pear trees
Ribes sylvestre redcurrants
Ribes uva-crispa
Ricinus communis
Saccharum officinarum - sugar cane
Secale cereale rye
Sesamum indicum sesame
Solanum tuberosum Irish potatoes
2C
Sorghum bicolor (s. vulgare) grain sorghum
Sorghum dochna
Spinacia oleracea spinach
Theobroma cacao cacao plants
Trifolium pratense red clover
Triticum aestivum wheat
Vaccinium corymbosum blueberries
- 12 -

9 9 O.Z. 0050/033878
Botanical name _ Common name
Vaccinium vitis-idaea cranberries
Vicia faba tick beans
Vigna sinensis (V. unguiculata) cow peas
Vitis vinifera grapes
Zea mays Indian corn~ sweet corn,
maize
The new arylthiolcarbamates may be mixed with each other,
or with numerous representatives of other herbicidal or growth-
-regulating active ingredient groups, and applied in such com-
binations. These combinations extend the spectrum of action,
and synergistic effects are sometimes achieved. Examples of com-
pounds which may be admixed are diazines, N-phenylcarbamates,
thiolcarbamates, diurethanes, halocarboxylic acids, phenoxy
fatty acids, triazines, amides, ureas, diphenyl ethers, tri-
azinones, uracils, benzofuran derivatives, etc. A number of
active ingredients which, together with the new compounds, give
mixtures useful for widely varying applications are listed below
by way of example.
2C ~-amino-4-chloro-2-phenyl-3(2H)-pyridazinone
5-amino-4-bromo-2-phenyl-3(2H)-pyridazinone
5-amino-4-chloro-2-cyclohexyl-3(2H)-pyridazinone
5-amino-4-bromo-2-cyclohexyl-3(2H)-pyridazinone
. 5-methylamino-4-chloro-2-(3-trifluoromethylphenyl)-3(2H)-
: -pyridazinone
5-methylamino-4-chloro-2-(3 ,~.,~ ,R,R-tetra~luoroethoxyphenyl)-
-3(2H)-pyridazinone
- 13 -

~ 25~9 O.Z. 0050/033878
5-dimethyl~;no-4-chloro-2-phenyl-3t2H)-pyridazinone
4,5-dimethoxy-2-phenyl-3(2H)-pyridazinone
4,5-dimethoxy-2-cyclohexyl-3(2H)-pyridazinone
4,5-dimethoxy-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone
5-methoxy-4-chloro-2-~3-tri~luoromethylphenyl)-3t2H)-pyridazinone
5-amino-4-bromo-2(3-methylphenyl)-3(2H)-pyridazinone
3-(1-methylethyl)-lH-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide
and salts
10 3-(1-methylethyl)-8-chloro-lH-2,1,3-benzothiadiazin-4(3H)-one-
-2,2-dioxide and salts
3-(1-methylethyl)-8-fluoro-lH-2,1,3-benzothiadiazin-4(3H)-one-
-2,2-dioxide and salts
3-(1-methylethyl)-8-methyl-lH-2,1,3-benzothiadiazin-4(3H)-one-
-2,2-dioxide and salts
l-methoxymethyl-3-tl-methylethyl)-2,1,3-benzothiadiazin-4(3H)-
-one-2,2-dioxide
1-methoxymethyl-8-chloro-3-(1-methylethyl)-2,1,3-benzothia-
dia~.in-4(3H)-one-2s2-dioxide
2C 1-methoxymethyl-8-fluoro-3-(1 methylethyl)-2,1,3-benzothiadiazin-
-4(3H)-one-2,2-dioxide
1-cyano-8-chloro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-
-one-2,2-dioxide
1-cyano-8-f~uoro-3-(1-methylethyl)-2,1,3-benzothiadiazin 4(3H)-
-one-2,2-dioxide
1-cyano-8-methyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-
: -one-2,2-dioxide
- 14 -

113ZS99 o.z. 0050/033878
1-cyano-3-tl-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-
-dioxide
1-azidomethyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-
-one-2,2-dioxide
3-(1-methylethyl)-lH-pyridino-[3,2-e]-2,1,3-thiadiazin-(4)-one-
-2,2-dioxide
N-(1-ethylpropyl)-2,6-dinitro-3,4-dimethylaniline
N-(1-methylethyl)-N-ethyl-2,6-dinitro-4-tri~luoromethylaniline
N-n-propyl-N-~-chloroethyl-2,6-dinitro-4-trifluoromethyl-
aniline
N-n-propyl-N-cyclopropylmethyl-2,6-dinitro-4-tri~luoromethyl-
aniline
N-bis-(n-propyl)-2,6-dinitro-3-amino-4-trifluoromethylaniline
N-bis-(n-propyl~-2,6-dinitro-4-methylaniline
N-bis-(n-propyl)-2,6-dinitro-4-methylsulfonylaniline
N-bis-(n-propyl)-2,6-dinitro-4-aminosulfonylaniline
bis-(B-chloroethyl)-2,6-dinitro-4-methylaniline
N-ethyl-N-(2-methylallyl~-2,6-dinitro-4-trifluoromethylaniline
2C 3,4-dichlorobenzyl N-methylcarbamate
2,6-di-tert.butyl-4-methylphenyl N-methylcarbamate
isopropyl N-phenylcarbamate
3-methoxyprop-2-yl N-3-fluorophenylcarbamate
isopropyl N-3-chlorophenylcarbamate
but-1-yn-3-yl N-3-chlorophenylcarbamate
4-chlorobut-2-yn-1-yl N-3-chlorophenylcarbamate
- 15 -

1132S~
o. z. 0050/033878
methyl N-3, 4-dichlorophenylcarbamate
methyl N-(4-aminobenzenesulfonyl)-carbamate
O-(N-phenylcarb~moyl)-propanone oxime
N-ethyl-2-(phenylcarbamoyl)-oxypropionic acid amide
3 ~ -N-isopropylcarbamoyloxypropionanilide
ethyl-N-(3-(N~-phenylcarbamoyloxy)-phenyl)-carbamate
methyl-N-(3-(N'-methyl-N'-phenylcarbamoyloxy)-phenyl)-carbamate
isopropyl-N-(3-(N'-ethyl-N'-phenylcarbamoyloxy)-phenyl)-
-carbamate
- methyl-N-(3-~N'-3-methylphenylcarbamoyloxy)-phenyl)-carbamate
methyl-N-(3-(N'-4-~luorophenylcarbamoyloxy)-phenyl)-carbamate
methyl-N-(3-(N'-3-chloro-4-fluorophenylcarbamoyloxy)-phenyl)-
-carbamate
ethyl-N-~3-N'-(3-chloro-4-fluorophenylcarbamoxyloxy)-phenyl]-
-carbamate
ethyl-N-~3-N'-(3,4-difluorophenylcarbamoyloxy)-phenyl]-carbamate
methyl;N-~3-(N'-3,4-difluorophenylcarbamoyloxy)-phenyl~-carbamate
2C
methyl N-3-(4'-fluorophenoxycarbonylamino)-phenylcarbamate
ethyl N-3-(2'-methylphenoxybarbonylamino)-phenylcarbamate
methyl N-3-(4'-fluorophenoxycarbonylamino)-phenylthiolcarbamate
methyl N-3-(2',4',5'-trimethylphenoxycarbonylamino)-phenylthiol-
carbamate
methyl N-3-(phenoxycarbonylamino)-phenylthiolcarbamate
- 16 -

. ~13Z599 o. z . 0050t033878
p-chlorobenzyl N,N-diethylthiolcarbamate
ethyl N,N-di-n-propylthiolcarbamate
n-propyl N,N-di-n-propylthiolcarbamate
2,3-dichloroallyl N,N-diisopropylthiolcarbamate
2,3,3-trichloroallyl N,N-diisopropylthiolcarbamate
3-methyl-5-isoxazolylmethyl N,N-diisopropylthiolcarbamate
3-ethyl-5-isoxazolylmethyl N,N-diisopropylthiolcarbamate
ethyl N,N-di-~ec.-butylthiolcarbamate
benzyl N,N-di-sec.-butylthiolcarbamate
ethyl N-ethyl-N-cyclohexylthiolcarbamate
ethyl N-ethyl-N-bicyclo-[2.1.1]-heptylthiolcarbamate
S-(2,3-dichloroallyl)-(2,2,4-trimethylazetidine)-1-carbothiolate
S-(2,3,3-trichloroallyl)-(2,2,4-trimethylazetidine)-1-carbothiolate
S-ethylhexahydro-1-H-azepine-1-carbothiolate
S-benzyl-(3-methylhexahydro-1-H-azepine-1)-carbothiolate
S-benzyl-(2,3-dimethylhexahydro-1-H-azepine-1)-carbothiolate
S-ethyl-(3-methylhexahydro-1-H-azepine-1)-carbothiolate
.
n-propyl N-ethyl-N-n-butylthiolcarbamate
2C 2-chloroallyl N,N-dimethyldithiocarbamate
N-methyldithiocarbamic acid~ sodium salt
trichloroacetic acid, sodium salt
dichloropropionic acid, sodium salt
~,~-dichlorobutyric acid, sodium salt
,B-tetrafluoropropionic acid, sodium salt
~-methyl-~-dichloropropionic acid, sodium salt
methyls~-chloro-~-(4-chlorophenyl)-propionate
- 17 -

5~
O.Z. 0050/033878
methyl ~ dichloro-~-phenylpropionate
benzamido oxyacetic acid
2,3,5-triiodobenzoic acid (salts, esters, amides)
2,3,6-trichlorobenzoic acid (salts, esters, amides)
2,3,5,6-tetrachlorobenzoic acid (salts, esters, amides)
2-methoxy-3,6-dichlorobenzoic acid (salts, esters, amides)
2-methoxy-3,5,6-trichlorobenzoic acid (salts, esters, amides)
3-amino-2,5,6-trichlorobenzoic acid (salts, eæters, amides)
0,S-dimethyltetrachlorothioterephthalate
10 dimethyl-2,3,5,6-tetrachloroterephthalate
disodium 3,6-endooxohexahydrOphthalate
4-amino-3,5,6-trichloropicolinic acid (salts)
ethyl 2-cyano-3-(N-methyl-N-phenyl)-aminoacrylate
isobutyl 2-~4-(4'-chlorophenoxy)-phenoxy]-propionate
me~hyl 2-[4-(2'~4'-dichlorophenoxy)-phenoxy]-propionate
methyl 2-C4-(4'-trifluoromethylphenoxy)-phenoxy]-propionate
2-~4-(2'-chloro-4~-trifluorophenoxy)-phenoxy]-propionic acid,
.~
sodium salt
2-~4-(3',5'-dichloropyridyl-2-oxy)-phenoxy]-propionic acid,
2C sodium salt
ethyl 2-(N-benzoyl 3,4-dichlorophenylamino)-propionate
methyl 2-(N-benzoyl-3-chloro-4-rluorophenylamino)-propionate
isopropyl 2-(N-benzoyl-3-chloro-4-fluorophenylamino)-propionate
2-chloro-4-ethylamino-6~isopropylamino-1,3,5-triazine
2-chloro-4-ethylamino-6-(amino-2~-propionitrile)-1,3,5-triazine

~i325~ o.z. 0050~033878
2-chloro-4 ethylamino-6-(2-methoxypropyl)~2-amino 1,3,5-
-triazine
2-chloro-4-ethylamino 6-butyn-1-yl-2-amino-1,3,5-triazine
2-chloro-4,6-bisethylamino-1,3~5-triazine
2-chloro-4,6-bisisopropylamino-1,3,5-triazine
2-chloro-4-isopropylamino-6-cyclopropylamino-1,3,5-triazine
2-azido-4-methylamino-6-isopropylamino-1,3,5-triazine
2-methylthio-4-ethylamino-6-isopropylamino-1,3,5-triazine
2-methylthio-4-ethylamino-6-tert.butylamino-1,3,5-triazine
2-methylthio-4,6-bi~ethylamino-1,3,5-triazine
2-methylthio-4,6-bisisopropylamino-1,3,5-triazine
2-methoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine
2Omethoxy-4,6-bisethylamino-1,3,5-triazine
2-methoxy-4,6-bisisopropylamino-1,3,5-triazine
4-amino-6-tert.butyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one
4-amino-6-phenyl-3-methyl 4,5-dihydro-1,2,4-triazin~5-one
4-isobutylidenamino-6-tert.butyl-3-methylthio-4,5-dihydro-1,2,4-
2C -triazin-5-one
1-methyl-3-cyclohexyl-6-dimethylamino-1,3,5-triazin-2,4-dione
3-tert.butyl-5-chloro-6-methyluracil
3-tert.butyl-5-bromo-6-methyluracil
3-isopropyl-5-bromo-6-methyluracil
3-sec.butyl-5-bromo-6-methyluracil
3-(2-tetrahydropyranyl)-5-chloro-6methyluracil
-- 19 --

113~599 o. z . oo50/033878
3-(2-tetrahydropyranyl)-5,6~trimethyleneuracil
3-cyclohexyl-5,6-trimethyleneuracil
2-methyl-4-(3'-trifluoromethylphenyl)-tetrahydro-1,2,4-oxa-
diazine-3,5-dione
2-methyl-4-(4'-fluorophenyl)-tetrahydro-1,2,4-oxadiazine-3,5-
-dione
3-amino-1,2,4-triazole
1-allyloxy-1-(4-bromophenyl)-2-[1',2',4'-triazolyl-(1')~-
-ethane (salts)
1-~4-chlorophenoxy)-3,3-dimethyl~1-(lH-1,2,3-triazol-1-yl)-
-butan-2-one
N,N-diallylchloroac.etamide
N-isopropyl-2-chloroacetanilide
N-(but-1-yn-3-yl)-2-chloroacetanilide
2-methyl-6-ethyl-N-propargy1-2-chloroacetanilide
2-methyl-6-ethyl-N-ethoxymethyl-2-chloroacetanilide
2-methyl-6-ethyl-N-t2-methoxy-1-methylethyl)-2-chloroacetanilide
2C 2-methyl-6-ethyl-N-(isopropoxycarbonylethyl)-2-chloroacetanilide
2-methyl-6-ethyl-N-(4-methoxypyrazol-1-yl-methyl)-2-chloro-
-acetanilide
2-methyl-6-ethyl-N-(pyrazol-1-yl-methyl)-2-chloroacetanilide
2,6-dimethyl-N-(pyrazon-1-yl-methyl)-2-chloroacetanilide
2,6-dimethyl-N-(4-methylpyrazol-1-yl-methyl)-2-chloro-acetanilide
2,6-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-2-chloroacetanilide
- 20 -

113Z5~9 o. z . 005~033878
2,6-dimethyl-N-(3,5-dimethylpyrazol-1-yl-methyl)-2-chloro-
acetanilide
2,6-dimethyl-N-(1,3-dioxolan-2-yl-methyl)-2-chloroacetanilide
2,6-dimethyl-N-(2-methoxyethyl)-2-chloroacetanilide
2,6-dimethyl-N-isobutoxymethyl-2-chloroacetanilide
2,6-diethyl-N-methoxymethyl-2-chloroacetanilide
2,6-diethyl-N-n-butoxymethyl-2-chloroacetanilide
2,6-diethyl-N-ethoxycarbonylmethyl-2-chloroacetanilide
2,3,6-trimethyl-N-(pyrazol-1-yl-methyl)-2-chloroacetanilide
2,3-dimethyl-N-isopropyl-2-chloroacetanilide
2-(2-methyl-4-chlorophenoxy-N-methoxyacetamide
2-~-naphthoxy)-N,N-diethylpropionamide
2,2-diphenyl-N,N-dimethylacetamide
d-(3~4~5-tribromopyrazol-l-yl)-N~N-dimethylpropionanlide
N-(1,1-dimethylpropynyl)-3,5-dichlorobenzamide
N-1-naphthylphthalamic acid
propionic acid 3,4-dichloroanilide
cyclopropanecarboxylic acid-3,4-dichloroanilide
2C methacrylic acid 3,4-dichloroanilide
2-methylpentanecarboxylic acid 3,4-dichloroanilide
N-2,4-dimethyl-5-(trifluoromethyl)-sulfonylaminophenylacetamide
N-4-methyl-5-(trifluoromethyl)-sulfonylaminophenylacetamide
2-propionylamino-4-methyl-5-chlorothiazole
0-(methylsulfonyl~-glycolic acid-N-ethoxymethyl-2,6-dimethyl-
anilide
- 21 -

~ Z5~3~ o. z . 0050/033878
0-(methylaminosul~onyl)-glycolic acid-N-isopropylanilide
0-(isopropylaminosul~onyl)-glycolic acid-N-but-1-yn-3-yl-anilide
0-(methylaminosulfonyl)-glycolic acid hexamethyleneamide
2,6-dichlorothiobenzamide
2,6-dichlorobenzonitrile
3,5-dibromo-4-hydroxybenzonitrile (salts)
3,5-diiodo-4-hydroxybenzonitrile (salts)
3,5-di~romo-4-hydroxy-0-2,4-dinitrophenylbenzaldoxime (salts)
3,5-dibromo-4-hydroxy-0-2-cyano-4-nitrophenylbenzaldoxime
(salts)
pentachlorophenol, sodium salt
2,4-dichlorophenyl-4'-nitrophenyl ether
2,4,6-trichlorophenyl-4'-nitrophenyl ether
2-fluoro-4,6-dichlorophenyl-4'-nitrophenyl ether
2-chloro-4-tri~luoromethylphenyl-4'-nitrophenyl ether
2,4'-dinitro-4-trifluoromethyl-diphenyl ether
2,4-dichlorophenyl-3'-methoxy-4'-nitro-phenyl ether
2-chloro-4-trifluoromethylphenyl-3'-ethoxy-4'-nitro-phenyl ether
2-chloro-4-tri~luoromethylphenyl-3'-carboxy-4'-nitro-phenyl
2C ether (salts)
2,4-dichlorophenyl-3'-methoxycarbonyl-4'-nitro-phenyl ether
2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione
2-(3-tert.butylcarbamoyloxyphenyl)-4-methyl-1,2,4-oxadiazolidine~
-3,5-dione
2-(3-isopropylcarbamoyloxyphenyl)-4-methyl-1,2,4-oxadiazolidine-
-3,5-dione
2-phenyl-3,1-benzoxazinone-(4)
- 22 -

1~3~9
O.Z. 0050/033878
(4-bromophenyl)-3,4,5,9,10-pentaazatetracyclo-[5,4,1,02'5'0,8'11]-
-dodeca-3,9-diene
2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranylmethane sul~onate
2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzo~uranyldimethylamino-
sul~ate
2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl-(N-methyl-N-
-acetyl)-aminosulfonate
3,4-dichloro-1,2-benzisothiazole
N-4-chlorophenyl-allylsuccinimide
2-methyl-4,6-dinitrophenol (salts, esters)
2-sec.butyl-4,6-dinitrophenol (salts, esters)
2-sec.bu~yl-4,6-dinitrophenol acetate
2-tert.butyl-4,6-dinitrophenol acetate
2-tert.butyl-4,6-dinitrophenol (salts)
2-tert.butyl-5-methyl-4,6-dinitrophenol (salts)
2-tert.butyl-5-methyl-4,6-dinitrophenol acetate
2-sec.amyl-4~6-dinitrophenol (salts, esters)
~ -dimethylbenzyl)-3-(4-methylphenyl)-urea
2C 1-phenyl-3-(2-methylcyclohexyl)-urea
1-phenyl-1-benzoyl-3,3-dimethylurea
1-(4-chlorophenyl)-1-benzoyl-3,3-dimethylurea
1-(4-chlorophenyl)-3,3-dimethylurea
1-(4-chlorophenyl)-3-methyl-3-but-1-yn-3-yl-urea
1-(3,4-dichlorophenyl)-3,3-dimethylurea
1-(3,4-dichlorophenyl)-1-benzoyl-3,3-dimethylurea
1-(3,4-dichlorophenyl)-3-methyl-3-n.butylurea
- 23 -

113Z5~9
O.Z. 0050J033878
1-(4-isopropylphenyl)-3~3-dimethylurea
1-(3-tri~luoromethylphenyl)-3~3-dimethylurea
1-(c~,d~R,~-tetrafluoroethoxyphenyl) 3,3-dimethylurea
1-(3-tert.butylcarbamoyloxyphenyl)-3,3-dime~hylurea
1-(3-chloro-4-methylphenyl)-3,3-dimethylurea
1-(3-chloro-4-methoxyphenyl)-3,3-dimethylurea
1-(3,5-dichloro-4-methoxyphenyl)-3,3-dimethylurea
1-[4-(4'-chlorophenoxy)-phenyl]-3,3-dimethylurea
1-~4-(4'-methoxyphenoxy)-phenyl]-3,3-dimethylurea
~ 1-cyclooctyl-3,3-dimethylurea
1-(hexahydro-4,7-methanoindan-5-yl)-3,3-dimethylurea
1-[1- or 2-(3a,4,5,7,7a-hexahydro)-4,7-methanoindanyl]-3,3-di-
methylurea
1-(4-rluorophenyl)-3-carboxymethoxy-3-methylurea
1-phenyl-3-methyl-3-methoxyurea
1-(4-chlorophenyl)-3-methyl-3-methoxyurea
1-(4-bromophenyl)-3-methyl-3-methoxyurea
1-(3,4-dichlorophenyl~-3-methyl-3-methoxyurea
2C 1-(3-chloro-4-bromophenyl)-3-methyl-3-methoxyurea
1-(3-chloro-4-isopropylphenyl)-3-methyl-3-methoxyurea
1-(3-chloro-4-methoxyphenyl)-3-methyl-3-methoxyurea
1-(3-tert.butylphenyl)-3-methyl-3 methoxyurea
1-(2-benzthiazolyl)-1,3-dimethylurea
1-(2-benzthiazolyl)-3-methylurea
1-(5-tri~luoromethyl-1,3,4-thiadiazolyl)-1,3-dimethylurea
imidazolidin-2-one-1-carboxylic acid isobutylamide
- 24 -

ll~Z599
o . Z . 0050/03387g
1,2-dimethyl-3,5-diphenylpyrazolium-methylsulfate
1,2,4-trimethyl-3,5-diphenylpyrazolium-methylsul~ate
1,2-dimethyl-4-bromo-3,5-diphenylpyrazolium-methylsul~ate
1,3-dimethyl-4-(3,4-dichlorobenzoyl)~5-(4-methylphenylsul~onyloxy)-
-pyrazole
2,3,5-trichloropyridinol-(4)
1-methyl-3-phenyl-5-(3'-trifluoromethylphenyl)-pyridone-(4)
1-methyl-4-phenylpyridinium chloride
1,1-dimethylpyridinium chloride
3-phenyl-4-hydroxy-6-chloropyridazine
- 1,1'-dimethyl-4,4'-dipyridylium-di(methylsul~ate)
1,1'-di-~3,5-dimethylmorpholine-carbanylmethyl)-4,4'-dipyridylium
dichloride
1,1'-ethylene-2,2'-dipyridylium dibromide
3-[1-(N-ethoxyamino)-propylidene]-6-ethyl-3,4-dihydro-2H-pyran-
-2,4-dione
3-~1-(N-allyloxyamino)-propylidene]-6-ethyl-3,4-dihydro-2H-pyran-
-2,4-dione
2-~1-(N-allyloxyamino)-propylidene]-~,5-dimethylcyclohexane-1,3-
2C -dione (salts~
2-~ allyloxyamino-butylidene]-5,5-dimethylcyclohexane-1,3-
-dione (salts)
2-[1-(N-allyloxyamino-butylidene]-5,5-dimethyl-4-methoxycarbonyl-
-cyclohexane-1,3-dione (salts)
2-chlorophenoxyacetic acid (salts, esters, amides)
4-chlorophenoxyacetic acid (salts, esters~ amides)
2,4-dichlorophenoxyacetic acid (salts, esters, amides)
- 25 -

1~32S~9
o . z . 0050/033878
2,4,5-trichlorophenoxyacetic acid (salts, esters, amides)
2-methyl-4-chlorophenoxyacetic acid (salts, esters, amides)
3,5, 6-trichloro-2-pyridinyl-oxyacetic
acid (salts, esters, amides)
methyl O~-naphthoxyacetate
2-(2-methylphenoxy)-propionic acid (salts, esters, amides)
2-(4-chlorophenoxy)-propionic acid (salts, esters, amides)
2-(2,4-dichlorophenoxy)-propionic acid (salts, esters, amides)
2-(2,4,5-trichlorophenoxy)-propionic acid (salts, esters, amides)
2-(2-methyl-4-chlorophenoxy)-propionic acid (salts, esters, amides)
4-(2,4-dichlorophenoxy)-butyric acid (salts, esters, amides)
4-(2-methyl-4-chlorophenoxy)-butyric acid (salts, esters, amides)
cyclohexyl-3-(2,4-dichlorophenoxy)~-acrylate
9-hydroxyfluorenecarboxylic acid-.(9) (salt esters)
2,3,6-trichlorophenylacetic acid (salts, esters)
4-chloro-2-oxobenzothiazolin-3-yl-acetic acid (salt~, esters)
gibelleric acid (salts)
disodium methylarsonate
2C monosodium salt o~ methylarsonlc acid
N-phosphonomethyl-glycine (salts)
N,N-bis-(phosphonomethyl)-glycine (salts)
2-chloroethyl 2-chloroethanephosphonate
ammonium-ethyl-carbamoyl-phosphonate
di-n-butyl-1-n-butylamino-cyclohexyl-phosphonate
- trithiobutylphosphite
O, O-diisopropyl-5- ( 2-benzosulfonylaminoethyl)-phosphorodithionate
- 26 -

113~5~9 o. z. 0050/0~3878
2,3-dihydro-5,6-dimethyl-1,4-dithiin-1,1,4,4-tetraoxide
5-tert.butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxa-
diazolone-(2)
4,5-dichloro-2-trifluoronethylbenzimidazole (salts)
1,2,3,6-tetrahydropyrid~zine-3,6-dione (salts)
succinic acid monc~N-dimethylhydrazide (salts)
(2-chloroethyl)-trimethylammonium chloride
(2-methyl-4-phenylsulronyl)-trifluoromethanesulrone anilide
1,1-dimethyl-4,6-diisopropyl-5-indanyl ethyl ketone
sodium chlorate
- am~onium thiocyanate
calcium cyanamide.
It may also be useful to apply the active ingredients,
either alone or in combination with other herbicides,in admixture
with other crop protection agents, e.g., agents for combating
pests or phytopathogenic fungi or bacteria. The compounds may
also be mixed with solutions o~ mineral matters used to remedy
nutritional or trace element deficiencies. Oils and oil con-
centrates of various types, wetting agents, spreader-stickers
2C and antifoams may be added to the individual active ingredients
or mixtures thereof.
Application may be e~fected for instance in the form of
directly sprayable solutions, powders, suspensions, dispersions,
emulsions, oil dispersions, pastes, dusts, broadcasting agents,
or granules by spraying, atomizing, dusting,- broadcasting or
watering. The ~orms Or application depend entirely on the pur-
pose for which the agents are being used; in any case they
- 27 -

:113Z5~9 o.z. 0050/033878
should ensure as fine a distribution of the active ingredient as
possible.
For the preparation of solutions, emulsions, pastes and
oil dispersions to be sprayed direct, mineral oil fractions of
medium to high boiling point, such as kerosene or die el oil,
further coal-tar oils, and oils of vegetable or animal origin,
aliphatic, cyclic and aromatic hydrocarbons such as benzene,
toluene, xylene, paraffin, tetrahydronaphthalene, alkylated
naphthalenes and their derivatives such as methanol, ethanol,
propanol, butanol, chloroform, carbon tetrachloride, cyclo-
hexanol, cyclohexanone, chlorobenzene, isophorone, etc., and
strongly polar solvents such as dimethylformamide, dimethyl-
sulfoxide, N-methylpyrrolidone, water, etc. are suitable.
Aqueous formulations may be prepared from emulsion con-
centrates, pastes, oil dispersions or wettable powders by
adding water. To prepare emulsions, pastes and oil dispersions
the ingredients as such or dissolved in an oil or solvent may be
homogenized in water by means Or wetting or dispersing agents,
adherents or emulsifiers. Concentrates which are suitable for
2C dilution with water may be prepared from active ingredient,
wetting agent, adherent, emulsifying or dispersing agent and
possibly solvent or oil.
Examples of surfactants are: alkali metal, alkaline earth
metal and ammonium salts of ligninsulfonic acid, naphthalene-
sulfonic acids, phenolsulfonic acids, alkylaryl sulfonates,
alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline
earth metal salts of dibutylnaphthalenesulfonic acid, lauryl
- 28 -

. 113~599 o . ~ . 0050/03387~
ether sulfate, fatty alcohol sulfates, alkali metal and alkaline
earth metal salts of fatty acids, salts of sulfated hexadecanols,
heptadecanols, and octadecanols, salts of sulfated fatty alco-
hol glycol ethers, condensation products of sul~onated naphtha-
lene an~ naphthalene derivatives with formaldehyde, condensation
products of naphthalene or naphthalenesulfonic acids with phenol
and ~ormaldehyde, polyoxyethylene octylphenol ethers, ethoxyl-
ated isooctylphenol, ethoxylated octylphenol and ethoxylated
nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
polyglycol ethers, alkylaryl polyether alcohols, isotridecyl
alcohol, fatty alcohol ethylene oxide condensates, ethoxylated
castor oil~ polyoxyethylene alkyl ethers, ethoxylated polyoxy-
propylene, lauryl alcohol polyglycol ether acetal, sorbitol
esters, lignin, sulfite wa~te liquors and methyl cellulose.
Powders, dusts-and broadcasting age~ts may be prepared by
mixing or grinding the active ingredients with a solid carrier.
Granules, e.g., coated, impregnated or homogeneous gra-
nules, may be prepared by bondin~ the active ingredients to
solid carriers. Examples of ~olid carriers are mineral earths
2C such as Rilicic acid, silica gels, silicates, talc, kaolin,
Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite,
diatomaceous earth, calcium sulfate, magnesium sulfate, mag-
nesium oxide, ground plastics, fertilizers such as ammonium
sulfate, ammonium phosphate, ammonium nitrate, and ureas, and
vegetable products such as grain flours, bark meal, wood ~eal,
and nutshell meal, cellulosic powders, etc.
- 29 -

1~3Z5~9 o.z. 0050/033878
q~
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D J~ ~ W Q,
O ~ h ~ h aJrl ~ o o rl h rl O O
E~ m ¢ ¢ c~ z o
- 30 -

ll~Z~9~
o~ z . 0050~033878
S
In
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~13Z599
o.z~ oo~o/033878
5,
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- 32 -

11325~3
O.Z. 0050/033878
Table 3 - Selective control of unwanted plants in Leguminosae;
postemergence treatment in the greenhouse
Compound no. 18
Appln. rate 0~25 kg~ha
Test plants Damage %
Arachis hypogaea 0
Glycine max 10
Amaranthus retroflexus 100
Centaurea cyanus 90
lO Digitaria sanguinalis 80
- Euphorbia geniculata 100
Poa annua 95
Sesbania exaltata 100
Stellaria media 98
~ _ . . . .
0 = no damage 100 = plants destroyed
2C

3'~ 5~ ~
O.Z. 0050~044878
Table 4 - Control of Sesbania exaltata in various crops;
postemergence treatment in the greenhouse
Compound no. 1
Test plants Damage %
_ Appln. rate0.25 0.5 kg/ha
Arachis hypogaea O O
Glycine max O O
Oryza sativa O O
Pisum sativum 10 15
lO Sorghum bicolor 0 15
- Sesbania exaltata 100 100
~ . . .. . .
O = no damage 100 - plantc completely destroyed
2C
- 34 -

1~325~
. ~. O~Z. 0050/033878
Table 5 - Selective weed control in Leguminosae;
; postemergence treatment in the greenhouse
Compound no. 29
Test ~lants _ Dama~e (~) at 0.5 kg/ha
Arachis hypogaea 0
. Glycine max ~0
Pisum sativum 10
Amaranthus retroflexus 100
Centaurea cyanus 80
10 Digitaria 3anguinalis 90
- Poa annua 90
Sesbania exaltata 100
Stellaria media 98
~ . . . . .
0 = no damage 100 = plants completely destroyed
2C

113ZS~
o. z . 0050/033878
Table 6 - Selective control of unwanted plants;
postemergence treatment in the greenhouse
Compound no. 54
Test plantsDamage (%) at 0. 5 kg/ha
Arachis hypogaea 0
Gossypium hirsutum 0
Amaranthus retroflexus100
Avena fatua 80
Digitaria sanguinalis 100
10 Euphorbia geniculata 100
Nicandra physaloides 100
Sesbania exaltata 100
Solanum nigrum 100
Stellaria media 98
.
O - no damage 100 = plants completely destroyed
2C
-- 36 --

3~ 5~ ~
O.Z. 0050/033878
Table 7 - Herbicidal action of further compounds;
postemergence treatment in the greenhouse
Compound kg~ha Test plants and damage (~)
no. IpomoeaCentaurea Lolium
spp. cYanus multiflorum
.
3.0 - 90
3.0 90 100 80
42 3.0 - 90 100
57 3.0 90 90 90
10 62 - 3.0 95 100
63 3.0 - 90 90
0 = no action 100 = plants completely destroyed
2C
~ 37 -

113Z5~3~ o.z. 0050/033878
EXAMPLE 3
90 parts by weight of compound 1 is mixed with 10 parts by
weight of N-methyl~-pyrrolidone. A mixture is obtained which is
suitable for application in the form of very fine drops.
EXAMPLE 4
20 parts by weight of compound 2 i~ dissolved in a mixture
consisting of 80 parts by weight of xylene, 10 parts by weight
of the adduct of 8 to 10 moles of ethylene oxide with 1 mole of
oleic acid-N-monoethanolamide, 5 parts by weight of the calcium
salt of dodecylbenzenesulfonic acid, and 5 parts by weight Or
-the adduct of 40 moles of ethylene oxide with 1 mole of castor
oil~. By pouring the solution into 100,000 parts by weight of
water and uniformly distributing it therein, an aqueous dis-
persion is obtained containing 0.02~ by weight of the acti~e
ingredient.
~XAMPhE 5
20 parts by weight of compound 3 is dissolved in a mix-
ture consisting o~ 40 parts by weight of cyclohexanone,
30 parts by weight o~ isobutanol, 20 parts by weight of the
2C adduct of 7 moles of ethylene oxide with 1 mole of isooctyl-
phenol~ and 10 parts by weight of the adduct of 40 moles of
ethylene oxide with 1 mole of castor oil. By pouring the solution
into 100,000 parts by weight of water and finely distributing
it therein, an aqueous dispersion is obtained containing 0.02%
by weight of the active ingredient.
-- 38 --

~ 1 3~ ~ ~
O.Z, 0050/033878
EXAMPLE 6
20 parts by weight of compound 1 is dissolved in a mix-
ture consisting of 25 parts by weight of cyclohexanol, 65 parts
by weight of a mineral oil fraction having a boiling point
between 210 and 280C, and 10 parts by weight of the adduct of
40 moles of ethylene oxide with 1 mole of castor oil. By pouring
the solution into 100,000 parts by weight of water and uniformly
distributing it therein, an aqueous dispersion is obtained
containing 0.02% by weight of the active ingredient.
EXAMPLE 7
- 20 parts by weight of compound 3 is well mixed with
3 parts by weight of the sodium salt of diisobutylnaphthalene-
~-sul~onic aci~, 17 parts by weight of the sodium salt of a
lignin sulfonic acid obtained from a sulfite waste liquor,
and 60 parts by weight of powdered silica gel, and triturated
in a hammer mill~ By uniformly distributing the mixture in
20,000 parts by weight of water, a spray liquor is obtained
contai~ing 0.1% by weight of the active ingredientO
EXAMPLE 8
2C 3 parts by weight of compound 3 is intimately mixed with
97 parts by weight of particulate kaolin. A dust is obtained
containing 3% by weight of the active ingredient.
EXAMPLE 9
30 parts by weight of compound 4 is intimately mixed
with a mixture consisting of 92 parts by weight of powdered
silica gel and 8 parts by weight of paraffin oil which has
been sprayed onto the surface of this silica gel. A formulation
of the active ingredient is obtained having good adherence.
~ 39 ~

~13Z5~39 o. z . 0050/033878
EXAMPLE 10
40 parts by weight of compound 1 is intimately mixed with
10 parts of the sodium salt of a phenolsulfonic acid-urea-form-
aldehyde condensate, 2 parts of silica gel and 48 parts of
water to give a stable, aqueous dispersion. Dilution in
100,000 parts by weight of water gives an aqueous dispersion con-
taining 0.04 wt~ o~ active ingredient.
EXAMPLE 11
20 parts o~ compound 2 is intimately mixed with 2 parts
of the calcium salt of dodecylbenzenesulfonic acid, 8 parts o~
a fatty alcohol polyglycol ether, 2 parts of the sodium salt
of a phenolsulfonic acid-urea-rormaldehyde condensake and
68 parts of a paraffinic mineral oil. A stable oily dispersion
is obtained.
2C
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